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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:04 UTC
HMDB IDHMDB15478
Secondary Accession NumbersNone
Metabolite Identification
Common NameBambuterol
DescriptionBambuterol is only found in individuals that have used or taken this drug. It is a long acting beta-adrenoceptor agonist used in the treatment of asthma. It is a prodrug of terbutaline.The pharmacologic effects of bambuterol are at least in part attributable to stimulation through beta-adrenergic receptors (beta 2 receptors) of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
Structure
Thumb
Synonyms
ValueSource
(+-)-5-(2-(Tert-butylamino)-1-hydroxyethyl)-m-phenylene bis(dimethylcarbamate)ChEBI
BambuterolumChEBI
Terbutaline bis(dimethylcarbamate)ChEBI
Terbutaline bisdimethylcarbamateChEBI
Bambuterol hydrochlorideHMDB
Chemical FormulaC18H29N3O5
Average Molecular Weight367.44
Monoisotopic Molecular Weight367.210721053
IUPAC Name3-[2-(tert-butylamino)-1-hydroxyethyl]-5-[(dimethylcarbamoyl)oxy]phenyl N,N-dimethylcarbamate
Traditional Namebambuterol
CAS Registry Number81732-46-9
SMILES
CN(C)C(=O)OC1=CC(=CC(OC(=O)N(C)C)=C1)C(O)CNC(C)(C)C
InChI Identifier
InChI=1S/C18H29N3O5/c1-18(2,3)19-11-15(22)12-8-13(25-16(23)20(4)5)10-14(9-12)26-17(24)21(6)7/h8-10,15,19,22H,11H2,1-7H3
InChI KeyInChIKey=ANZXOIAKUNOVQU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Adrenergic beta-Agonists
  • Bronchodilator Agents
  • Sympathomimetics
  • Tocolytic Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.69e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 mg/mLALOGPS
logP1.69ALOGPS
logP1.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.34 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity98.28 m3·mol-1ChemAxon
Polarizability40.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01408
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01408
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01408
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID49466
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBambuterol
NuGOwiki LinkHMDB15478
Metagene LinkHMDB15478
METLIN IDNot Available
PubChem Compound54766
PDB IDNot Available
ChEBI ID553827
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Gazic I, Bosak A, Sinko G, Vinkovic V, Kovarik Z: Preparative HPLC separation of bambuterol enantiomers and stereoselective inhibition of human cholinesterases. Anal Bioanal Chem. 2006 Aug;385(8):1513-9. Epub 2006 Jul 25. [16865342 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Rosberg B, Schroder C, Nyberg L, Rosenborg J, Wiren JE: Bambuterol and terbutaline in human cerebrospinal fluid and plasma. Eur J Clin Pharmacol. 1993;45(2):147-50. [8223836 ]
  2. Svensson LA: Bambuterol, a bronchodilator prodrug with sustained action, enhances delivery of active drug to the lung. Agents Actions Suppl. 1988;23:271-6. [3262993 ]
  3. Waldeck B: Beta-adrenoceptor agonists and asthma--100 years of development. Eur J Pharmacol. 2002 Jun 7;445(1-2):1-12. [12065188 ]
  4. Coleman RA, Johnson M, Nials AT, Vardey CJ: Exosites: their current status, and their relevance to the duration of action of long-acting beta 2-adrenoceptor agonists. Trends Pharmacol Sci. 1996 Sep;17(9):324-30. [8885698 ]
  5. Zhang D, Cheng M, Hyun MH, Xiong Z, Pan L, Li F: Enantiomeric separation of beta2-agonists on macrocyclic antibiotic chiral stationary phases in high performance liquid chromatography. Pharmazie. 2007 Nov;62(11):836-40. [18065099 ]
  6. Chou YL, Wu CC, Wang HW: Effects of bambuterol and terbutaline on isolated rat's tracheal smooth muscle. Eur Arch Otorhinolaryngol. 2010 Aug;267(8):1305-11. Epub 2009 Dec 12. [20012638 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]